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Top 20 Biggest Transfer Losses of All-Time

The transfer market can be a ruthless business. Vast sums of money are required to prise the top players in the world away from other clubs and as such, the weight of expectation upon these individuals is often measured by a transfer fee.

The services of the best in the business inherently demand the highest financial compensation, but a heavy burden comes with the accountability of earning the biggest pay packet at a club or being one of the most expensive footballers of all-time.

Like any industry, a footballer works to climb a professional ladder. Once a player lands a move to one of the biggest and wealthiest teams in the world, what happens next can shape the remainder of a career.

Some players enjoy years of success and grow old with the club while their market value naturally depreciates over time. These individuals can reimburse investment in the form of silverware, commercial opportunities and prestige before moving into the twilight of their playing days either for a small fee or nothing.

Conversely, others stumble from day one in their new office and find themselves scrambling to save a once promising career. Whether due to injury, personal issues or a lack of chemistry between colleagues, employers can't afford to hang on to deadwood. When expensive players aren’t performing, they will often be loaned out in a bid to recover their form or otherwise pushed through the door on a permanent basis.

This kind of situation can inflict crippling damage to a professional footballer’s reputation and market value. A cut-price sale to a suitor – if one exists – is usually the most amiable outcome for club and player.

Please note: These figures are sourced from transfermarkt.co.uk and players who retired after their last permanent transfer are not eligible to make this list.

With the criteria outlined, here are the top 20 biggest transfer losses of all-time.

20 Joleon Lescott to West Bromwich Albion – £19.25m Loss

Once a cult hero at Goodison Park, Joleon Lescott has lost his fair share of admirers since turning his back on the Everton faithful for the riches of Manchester City in August 2009. His then manager David Moyes ignored the want-away defender’s incessant pleas to let him go until the Sky Blues tabled an irresistible £19.25m offer. Despite collecting four trophies including two Premier League titles with City, Lescott never looked worthy of the huge fee the club paid to prise him away from Merseyside. The veteran defender was subsequently released at the conclusion of the 2013-14 season before West Bromwich Albion picked him up on a free transfer less than a month later.

19 T18. Anderson to Internacional – £22.05m Loss

It takes a seriously talented player to command a £22.05m transfer fee – let alone one who’s yet to celebrate his 20th birthday. Manchester United and Sir Alex Ferguson thought they had got their hands on a bona fide wonderkid when they shelled out an eight-figure sum to sign Anderson from FC Porto in May 2007. However, things didn’t turn out as expected for Anderson, who caught the eye for all the wrong reasons during a tumultuous seven-year spell at Old Trafford. A loan move to Fiorentina failed to awaken his reputed potential and he was eventually offered a career lifeline in the form of a free transfer to Internacional in February 2015.

18 T18. Denilson to Bordeaux – £22.05m Loss

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Although Denilson played for 10 different clubs over the course of his career, only one ever paid a transfer fee to secure his services. In 1998, Real Betis forked out £22.05m for the Sao Paulo prodigy – a deal that broke the world record figure at the time. After his parent club was relegated to the Segunda Division in 2000, the Brazilian was loaned to Flamengo for a season only to return the following January as Betis regained promotion to La Liga at the first time of asking. But Denilson found himself surplus to requirements after seven seasons with the Spanish outfit, and was allowed to join Bordeaux on a free transfer in the summer window of 2005.

17 Gabriel Batistuta to Al-Arabi – £22.75m Loss

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Besides the Argentinian national team, Fiorentina was the main beneficiary of Gabriel Batistuta’s illustrious career. After snapping up a free striker who went on to become the all-time leading goalscorer for one of the most successful nations in football history, the Viola pocketed a cool £22.75m when he signed for rivals AS Roma in July 2000. To sweeten the deal, the ageing Batistuta was already past his best when he arrived in Rome and struggled to replicate the deadly form he produced at his previous club. He was then loaned out to Inter Milan before joining Al-Arabi at no cost to the Qatari outfit and would ultimately retire in the Middle East.

16 Dimitar Berbatov to Fulham – £23.1m Loss

Not many top players can get away with strolling around the pitch in the manner Dimitar Berbatov once did. The Bulgarian striker was never one to grit his teeth and close down defenders in their own half, but his wizardry in other areas of the pitch well and truly made up for a lack of work ethic. Manchester United paid Tottenham Hotspur £26.6m to sign the classy hitman in September 2008 and although his impact wasn’t felt throughout his entire stint at Old Trafford, his trademark skill provided many memorable moments. After four patchy seasons with the Red Devils, Berbatov departed for £3.5m to join Fulham in August 2012.

15 Javier Saviola to Real Madrid – £25.13m Loss

Drawing comparisons with the great Diego Maradona places a heavy burden on any footballer. In the case of former River Plate starlet Javier Saviola, the weight of expectation seemingly became too much after completing his high-profile move to Barcelona at 19-years-old in July 2001. The diminutive striker contributed a 17-goal haul in his first season at the Nou Camp, but his promising start fell to pieces in a goal-dry second term. Saviola was shipped out on loan to AS Monaco and then Sevilla before Real Madrid negotiated a deal with him after his Barcelona contract expired in July 2007.

14 Lilian Thuram to Barcelona – £25.55m Loss

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Paying more than 25 million pounds seems like a good deal considering how important Lilian Thuram was to Juventus between 2001 and 2006. The Serie A giants offered Parma £29.05m to slot him into a fearsome defensive unit alongside Fabio Cannavaro, Gianluca Zambrotta and Jonathan Zebina, with Gianluigi Buffon in goal behind them. The French centre-back lifted the Scudetto twice with Juventus, but his club’s involvement in the 2006 Italian football scandal saw these titles revoked and the Old Lady automatically relegated to Serie B. The controversy triggered an exodus of star players including Thuram, who moved to Barcelona for a paltry £3.5m in July 2006.

13 Didier Drogba to Shanghai Shenhua – £25.9m Loss

Although Didier Drogba cost £25.9m to sign from Marseille in July 2004, many Chelsea fans rightly believe it’s impossible to put a price on his contribution to the club. He tucked home the penalty to win the Blues’ maiden Champions League crown, played a telling hand in each of the four Premier League triumphs during the past decade and scored countless decisive goals during his first spell at Stamford Bridge. Despite everything Drogba gave to his beloved Chelsea, it doesn’t change the fact he departed for Shanghai Shenua on a free transfer soon after the events in Munich in May 2012.

12 T11. Ronaldo to AC Milan – £26.25m Loss

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Never has the torment of injuries hindered a football career more so than that of the original Ronaldo. Widely regarded as one of the most gifted players of all-time, the Brazilian striker certainly reached the heights expected of him during his career, albeit temporarily. Despite his troublesome knees, Ronaldo arrived at Real Madrid in 2002 soon after winning his third World Player of the Year award. Although £31.5m seems like a bargain for even a half-fit Ronaldo, it’s disappointing he never managed to recapture the devastating form that earned him the nickname Il Fenomeno at Inter Milan. The iconic number nine spent four years in La Liga before joining AC Milan for £5.25m in January 2007.

11 T11. David Beckham to L.A Galaxy – £26.25m Loss

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It’s difficult to think of a single transfer that has caused more fuss across an entire nation than when David Beckham completed a free switch to Los Angeles Galaxy from Real Madrid in January 2007. The former Manchester United star, who joined the La Liga giants for £26.25m in July 2003, jetted to the U.S after playing four seasons alongside the likes of Ronaldo, Zinedine Zidane and Raul in Spain. Despite significant investment in the rest of the squad, Becks’ stint with Real fell short of the success he enjoyed at Old Trafford in terms of silverware. He lifted just a single league title with Los Blancos before leaving to help develop football in America.

10 David Villa to Atlético Madrid– £26.53m Loss

After spending five years as the star man at Valencia, David Villa became one of many superstars at the Camp Nou when he signed for £28m in May 2010. His quality was unquestionably equal to the players around him, but the Spaniard wasn’t afforded the same goalscoring freedom he thrived upon at the Mestalla. Credit to his clinical instincts in the box, Villa bagged 48 goals in 119 appearances in all competitions for the Blaugrana before he was sold to Atlético Madrid for a measly £1.47m in July 2013. Not a bad price for Spain’s all-time top goalscorer, is it?

9 Michael Essien to AC Milan – £26.6m Loss

Michael Essien was comfortably one of the best and most complete midfielders in the world during his peak years at Chelsea. Prior to suffering his first serious knee injury in September 2008, the Ghanian possessed the type of physical gifts only a handful of other players could compete with. Signing for £26.6m in August 2005, Essien became a key player for the Blues as they mounted a bid to tackle Europe’s elite; he ran the show in midfield and even popped up with the occasional – and often crucial – goal. His diminishing physical attributes saw him drift out of favour at Stamford Bridge before joining AC Milan once his contract expired in January 2014.

8 Zlatan Ibrahimović to AC Milan – £27.65m Loss

One of a kind players inherently command huge amounts of money in the transfer market. Zlatan Ibrahimovic is undoubtedly among the most unique players ever to grace a football pitch, so it’s not particularly surprising the collective amount of transfer fees paid to sign him exceeds all but one other, Angel Di Maria. The Swede has cost clubs £118.37m all up, the most expensive move of his career being when Barcelona parted with £48.65m to take him from Inter Milan in July 2009. A fractured relationship with Pep Guardiola prompted Ibrahimovic to seek a move elsewhere, and AC Milan successfully took him off Barca’s hands with a £21m bid.

7 Rui Costa to Benfica – £29.4m Loss

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Managers often bring their favorite personnel along when they switch clubs. Rui Costa was constantly linked with a move away from Fiorentina during his pomp, but a move only transpired when the club ran into financial troubles and then manager Fatih Terim took the reigns at AC Milan in the 2000-01 season. He paid £29.4m to lure the Portuguese creator to his new dressing room – making him the most expensive Milan player ever at the time. Rui Costa played five seasons with the Rossoneri and won the Serie A, Italian Cup and Champions League before the arrival of Kaká led to fewer minutes on the pitch and a return to Benfica following his release.

6 Gaizka Mendieta to Middlesborough – £30.1m Loss

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Having earned interest from a host of clubs around Europe while playing for Valencia, Gaizka Mendieta was bought by Lazio for £33.6m to fill the void left by outgoing playmakers Pavel Nedved and Sebastian Veron. He spent one full season playing in the Serie A before his employers elected to get him off the wage bill for the time being. Loan moves to Barcelona and then Middlesborough (which they at least received money for) became permanent when the Rome club allowed the Spaniard to join the latter on a free transfer in July 2004. Injuries marred his four-year stint in England and he eventually retired following the expiry of his contract in May 2008.

5 Andriy Shevchenko to Dynamo Kyiv – £30.31m Loss

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Andriy Shevchenko arrived at Chelsea for £35.7m from AC Milan under the expectation he would maintain the goalscoring proficiency that earned him a reputation as one the deadliest strikers on the planet. The Ukrainian, who finished his seven-year stint at the San Siro with 173 goals, failed to terrorize Premier League defenders with any kind of regularity. After two frustrating campaigns with the Blues, Shevchenko was loaned back to Milan in an attempt to stimulate his goalscoring instincts – a move that did more harm than good for his confidence. In August 2009, his Chelsea deal expired and he relocated to boyhood club Dynamo Kyiv, where he would spend three seasons before calling time on his career.

4 Christian Vieri to AC Milan – £31.5m Loss

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Christian Vieiri was one of the finest strikers in the world when Inter Milan shelled out £31.5m and broke the world transfer record to sign him from Lazio in July 1999. Possessing all the key attributes of a predatory striker, the Italian bagged 17 goals or more in each of his six campaigns with the Nerazzurri before strained relations with Roberto Mancini prompted the mutual termination of his contract in July 2005. AC Milan pounced on the unattached striker but saw the back of him within just six months as he joined AS Monaco in pursuit of regular football ahead of the 2006 World Cup.

3 Rio Ferdinand to Queens Park Rangers – £32.2m Loss

Manchester United hasn’t looked the same at the back since Rio Ferdinand left the club when his contract expired in July 2014. The £32.2m fee the Red Devils paid to secure his signature from Leeds United in 2002 is a just price considering his 12 years of exemplary service at Old Trafford. Ferdinand racked up 17 major honours at United before time took its toll on ageing centre-back’s legs and he could no longer marshall the backline with his trademark class. At 35-years-old, he elected to join Queens Park Rangers on a free transfer to play out one final top-flight campaign.

2 Fernando Torres to AC Milan – £38.85m Loss

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Chelsea was destined to lose a decent chunk of cash following the £40.95m signing of Fernando Torres and the four goal-shy seasons that ensued. Much to agony of the Stamford Bridge crowd, the Blues had seemingly signed a different striker to the one who struck fear into the hearts of defenders as the spearhead of Liverpool’s attack. Torres found the net during intermittent patches of promising form, but he never rediscovered the player he once was. His blue nightmare ended in January 2015 when AC Milan agreed to make his loan deal permanent by paying Chelsea a £2.1m fee.

1 Kaká to AC Milan – £45.5m Loss

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It’s hard to dispute that Kaká was one of the most mesmerising footballers on the planet at the height of his powers between 2003 and 2009 at AC Milan. As most top players due at some point during their career, the Brazilian caught the eye of Real Madrid with his unrivalled combination of speed, technique and skill. Milan officials simply couldn’t turn down the kind of money the Spanish giants were offering and reluctantly allowed Kaká to depart for £45.5m in July 2009.

However, the attacking midfielder failed to live up to the astonishing expectations he set at the San Siro and endured four seasons of lackluster displays in the famous all-white kit. With his time up in the cutthroat first-team at the Santiago Bernabeu, Kaká completed a romantic free transfer back to Milan in September 2013.